Extra Special Fun on New Year’s Eve

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Jack and his fiancé play around with her best friend.
14.7k words
4.67
27.1k
24

Part 1 of the 2 part series

Updated 06/15/2023
Created 11/02/2022
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Extra Special Fun on New Year's Eve

December 31st, New Year's Eve. My fiancé Katie and I were scrambling throughout the apartment to put the last minute touches up for our small party we were throwing to bring in the new year. We'd spent the day shopping for groceries, liquor, and all the cheesy New Year's decorations one would expect to find. We had streamers, noise machines, small funny hats, and even some banners to hang from the ceiling. For me, it was more than I would have done given that only one of our friends was coming over to celebrate with us. To Katie though, she always enjoyed planning and throwing parties, no matter the size. Seeing her excitement when we woke up that day and she went over her plans with me, there was no way I was going to take that from her.

"Hey Jack, can you finish hanging those banners while I get the charcuterie board finished," Katie yelled from the kitchen. I could hear the sound of her cutting something. Must have been cheese or sausage, I thought.

"Sure, I just need a second. The damn Wi-Fi has been cutting in and out all day and it's driving me crazy," I responded. I worked in the IT field, so this was normally my thing. However, this time around there was little I could do about the issue, which was becoming progressively apparent as I stormed off to my office to reboot the modem for a fourth time today.

As I opened the door to my office I caught a glimpse of myself in the mirror sitting in the corner across the room. When I say I had an office, it was more of a desk tucked away amidst a large collection of things that had no other place in the apartment. We only had about a thousand square feet, and Katie had been living in a house before we met so she'd accumulated a lot of stuff. I chuckled to myself after a moment of seeing the ridiculousness that I was portraying.

I'm not what you would call the most fit gentleman you'd ever met in your life, but I tried my best to keep in shape. I stood around six-foot tall, weighing in at about two-hundred fifty pounds. I wore glasses most times that framed my dark brown eyes, and I had a nicely-kept medium length full beard that trailed down from my sideburns, over my chin, and up around my mouth into a mustache. I liked to keep my hair somewhat short, but not buzzed. I just didn't like the trouble of washing and dealing with longer hair, especially in the wind when it would blow around and wind up sticking out every which way. I was wearing my regular pair of somewhat-worn-out blue jeans, and a dark blue button up. I chuckled when I caught a glimpse of the too-small black and gold top hat that was sitting on top of my head, with a thin black rubber band that came down around my chin to hold it there. Katie had put it on me when we were unpacking the decorations, and I must have forgotten about it.

"Jack, hurry up! Cori is going to be here in about thirty minutes," I heard Katie yell from the kitchen again.

"Okay, okay, I'm coming," I yelled back, reaching down to my desk to unplug the router. I waited about thirty seconds before plugging it back in, and watched the power light come on and start flashing. The normal boot up cycle that I was used to seeing. Normally, I stuck around to make sure the internet reconnected, but I wasn't about to have to make Katie ask a third time. I rushed out of my office, grabbed a chair from around our dining table, and got to work hanging the "Happy New Year" banner that we had bought. Standing on the chair from the angle I was at, I could see Katie in the kitchen putting the finishing touches on the charcuterie board. Katie was built similarly to me: not the thinnest girl you'd ever seen, but definitely more athletic. I had never been one to go for the thinnest girl anyway, given my own body. Katie's was perfect for me though. She stood at about five-foot three, with wide hips and long light brown hair that reached down to just barely kiss the top of her large, bubble-shaped ass. She was wearing black yoga pants that clung to her ass perfectly, and I could tell she was wearing a thong by the lack of a panty line as well as the way the fabric got sucked up into her butt crack, leaving the perfect outline. I lingered on her perfect ass for a few extra moments before looking back up her body again. She definitely didn't have a flat stomach, but again that was my preference. She wasn't afraid to eat, and that was one of the things that made me fall even more in love with her. Sitting just a few inches up were her massive - and I mean massive - G cup tits. The bra she was wearing under her sexy "party" shirt left little to the imagination as the way they pushed her tits together left a deep line of cleavage that I tended to admire even more than her ass at times. Some guys prefer ass, some prefer tits; I myself was a connoisseur of both, but I couldn't deny how much I loved seeing those huge tits bounce when I had Katie on her back. The thought was enough to get a slight twitch from my cock inside my pants.

Katie must have caught me staring, because the next thing I snapped out of my trance hearing her speaking directly at me, "Hey there mister, there will be time for ogling later. Hang that banner, and maybe I'll give you a reward." The wink that followed nearly killed me, and got another, far stronger, twitch from my cock. Katie definitely knew what turned me on, and exactly what buttons to push to tease me. We had talked about most of our sexual fantasies, kinks, and preferences when we first met. We both believed in having a strong sexual connection with your partner, and the role that it played in the relationship. By the time we had been dating even just a few weeks, we both had a good sense of what the other person really liked, and by God it showed. I don't like to brag too often, but our sex life was amazing. I had been with a few other partners before Katie, like she had been before me, but we both had agreed that none on either side could compare with the sexual chemistry we had with one another. I always had thought that the best way to experience truly amazing sex was to have a real connection with the other person, and after I had met Katie I knew that to be one-hundred percent correct.

I gulped almost too loudly after hearing what Katie had said, and quickly finished hanging the banner. I stepped off of the chair and took a few more steps back to admire my handiwork. The banner was perfectly positioned not far from the entrance landing to our apartment, and I enjoyed the fact that it had "Happy New Year" mirrored on both sides so it could be seen from the entrance and the rest of the living room.

"Well, what do you think," I asked, looking for the nod from Katie.

"Looks great," Katie replied as she stepped out of the kitchen and wrapped her arms around me from the side. She buried her face into my chest and rested her hand near my heart, before looking up at me with her big green eyes and gave me a sweet smile. I smiled back in kind, and leaned in to kiss her gently. Katie and I had been dating for over a year, and engaged for a few months, but every time we kissed I still got the same feeling in my body that I had felt the first time we'd done it. It sent shivers through me like nothing I'd ever felt before, and those shivers definitely extended down to below my belt as well. Our lips parted as we continued to kiss, slowly at first but before long we both could feel the passion increasing. Katie's tongue entered my mouth and I responded with my tongue wrapping around hers. I placed my hand on the back of her head and gave a gentle tug on the back of her hair, which broke our kiss for a moment as Katie's head leaned back and I heard her let out a soft moan. Like I said, I knew how to push her buttons just as well as she knew mine.

"You better be careful, mister. You're going to start something that we don't have much time to finish," Katie said seductively before letting out another quiet moan. I tightened my grip on her hair slightly, and leaned down to kiss her lips again. This time though, just before our lips touched I moved my mouth to her neck. Katie purred as I began kissing and sucking on her neck, running my tongue up to her earlobe and nibbling on it gently. "Ooooh," Katie moaned, "that's not fair."

Just as things were starting to heat up, I heard both of our phones go off with an incoming text notification. Katie and I both looked at each other, and while neither one said anything out loud, you could feel the simultaneous groan. Both of us receiving a text at the same time meant that it was in one of our group chats, and the only one we expected today was with the sole guest to our party: Katie's friend Cori.

"Yep, Cori's pulling into the complex now," Katie said, looking down at her phone.

"Damn," I said, "guess we'll have to put a pin in that for now."

"Oh don't you worry baby, you're going to be in trouble later for that little stunt you just pulled," Katie said slyly before giving me another one of those knee-buckling winks. Katie turned to head towards the door to our apartment, "accidentally" brushing her hand against what was now a rock hard boner in my pants. She looked back at me and gave me another smile, taking extra care to shake her big ass an extra few times as she sauntered towards the door.

Just as I was heading into the kitchen to pour myself a drink, I heard our phones go off again. This time I pulled my phone out of my pocket to check what it was about. It was another text from Cori: "Shot of tequila for when I get in please," it read.

"Oh damn, looks like Cori is ready to party," I chuckled as I put my phone down on the counter and reached up to the cupboard above our stove to grab three shot glasses. I lined the glasses up next to each other on the counter, and turned to the liquor cupboard to grab the bottle of Jose Cuervo we had set off to the side.

"Damn," Katie laughed, "yeah no kidding. Tequila too! Well, that's even better for you later." Katie was right. Tequila was one alcohol that definitely lived up to its reputation, where Katie was concerned. We didn't drink it often, but when we did it almost always led to some hot, frisky sex.

"Don't need to tell me twice," I said, "I'm already pouring!"

I popped the top off of the bottle and turned to pour the three shots, taking extra care to fill each glass as much as possible while still being able to lift them without spilling. Just as I finished topping off the last glass, I heard a knock at the door. Katie quickly unlocked it and immediately started shouting, "hey! Oh my god I'm so happy you made it! Come in, Jack's pouring our shots now!"

I collected all three glasses into my hands and turned around. When I saw Cori, I stopped in my tracks and nearly dropped the shots all over the kitchen floor. Cori was one of Katie's best friends, and I'd be lying if I said I didn't have many fantasies about her in the privacy of my office, or shower, or anywhere else I could get a few minutes to jack off. She was about the same height as Katie, maybe slightly taller. She had a very fit, tight body with small B cup tits. Her skin was a more olive complexion, and she too wore glasses that framed beautiful brown eyes. Hands down though the best thing about Cori was her ass. When I said she was fit, you could tell she took extra care to do her squats and stairmaster cardio at the gym. Her ass was smaller than Katie's, but extremely toned and perky. I swear, you could bounce a quarter off of it that would bounce halfway across the room. Cori too was wearing tight black yoga pants, and I couldn't help myself but to catch a glimpse of it as she turned around and bent down to take off her boots. I noticed that she too must have been wearing a thong, given that she also had a nice deep butt crack line. As she was taking off her boots, her body shifted slightly and the yoga pants hit the foyer light just right. I thought I was going to have to pick up my own jaw off of the floor when I noticed that the light had made her yoga pants partially see through. There, right before my eyes, was Cori's perfect ass, and sticking out in the light clear as day was a lacy, black thong. I didn't think it was possible for my cock to get harder than it already was, but somehow I felt the bulge in my pants press even more firmly against the fabric of my jeans.

Cori had finished taking off her boots and stood back up, turning around to face us. For a brief second, my face curled up in a dissatisfied scowl, wishing that I could have frozen time to see that view for eternity. Even Katie had commented multiple times how great Cori's ass was. That was another thing I had loved about her: she wasn't afraid to let me look at other girls. She knew that as a guy, even when we're fully committed in our relationships, when we see a drop dead gorgeous girl, we're going to look for at least a second. There had been multiple occasions where Katie was actually the first one to make a comment about the way a girl's ass looked, or how her top showed off a nice rack. There had even been a few drunken nights of sex where she would whisper dirty things in my ear about a girl we'd both seen at a night out. Katie had never been with a girl before, but even she thought that she was a little bi-curious, at least. We'd talked about threesomes before, and she had said that she wasn't totally against it, as long as it was with the right person.

"Oh my god, give me one of those please," Cori exclaimed as she finished hugging Katie and moved quickly over to me in the kitchen. I held out the collection of shot glasses, allowing Cori to pick which one she wanted. Cori gave me a sweet, friendly smile - a smile that made her look even cuter than she was when she walked it, if one could think that possible. Katie followed in behind her and I handed my fiance the other shot glass. Cori set hers down on the counter and came in to give me a hug.

"Where are my manners," Cori said, "I'm sorry Jack, I didn't mean to not hug you!" I spread my arms and Cori fell into them. I wrapped my arms around her in a sort of bear hug that I was known for, and we sat there for a few moments rocking back and forth on our feet. It wasn't until we were starting to pull away that I realized my cock was still rock hard in my pants! Oh my god, I thought. Did she feel that? We were definitely close enough. I tried to hide my embarrassment, but if Cori noticed she played it off like she didn't. For a second though, I thought I saw her eyes linger near my waistband before she turned back to grab her shot of tequila.

"Cheers!" We all raised our glasses and clanked them together before bringing them in and taking the shot. All three of us made a somewhat sourpuss face briefly before slamming our shot glasses down on the counter. Cori let out a loud "Wooo!" as she did, and we all laughed.

"So Cori," I started, "greeted with a shot of tequila. Anything you need to get off your chest?"

Cori laughed at my pathetic attempt at conversation - though to be fair, the blood that was supposed to be in my brain was still currently elsewhere. "Oh...well, I mean, yeah it's nothing too bad. I just had a date last night that didn't go so well," she said.

"Oh no," Katie exclaimed, "what happened?"

"Oh you know," Cori said, "typical guy who thinks he's hotter shit than he actually is. I mean, we had an okay time at dinner, but--" Cori cut herself short and flashed me a concerned look. "Sorry Jack if this is TMI but...we went back to my place and things seemed like they were getting hot and heavy. But when it came time for him to...perform, he couldn't."

I nearly choked on the bottle of water I was drinking from when Cori said that. I started coughing, and Katie and Cori both leaned in to pat me on the back to try and help me. "Oh babe, are you okay," Katie concerningly asked."

"Oh yeah, I'm fine," I said, finishing my coughing spell and taking another sip of water before I continued, "just definitely not what I was expecting you to say, Cori." No guy liked to hear about when another guy couldn't "get it up", it was just something that dudes didn't discuss. If I was being honest with myself though, I felt more sorry for Cori. She's a hot girl, no doubt, and if a guy couldn't get it up for her, I can't imagine he'd be able to get it up for anyone. "I'm sorry to hear that though. That must have been really frustrating."

"It was! Ugh, and I was so looking forward to getting laid too! It was the first time I'd had a chance in almost two months," Cori said, clearly annoyed at the situation. "So yeah, tonight I'm going to need to blow off some steam, so I'm planning on getting as drunk as possible. That started with this shot of tequila! You're the best for having it ready for me, by the way." Cori leaned in and wrapped one arm around my shoulders for a quick side hug. As she did, I felt one of her small, perky tits brush up against my chest. Wait, I thought, was that on purpose? No, it couldn't have been. That kind of thing happens all the time. It wasn't doing anything to help my situation in my pants though; I could practically feel my heartbeat through my cock.

"Um, I've gotta hit the bathroom," I said, "baby, would you mind making me a drink for when I get back?"

"Of course honey," Katie said. "Don't take too long," Katie winked at me quickly, and flashed a glance down to my hard on before turning around to grab a glass.

I rushed off to the bathroom, and I could hear Katie and Cori talking, but couldn't quite make out what they were saying. I was in a mad dash to the toilet to try and calm myself down. I shut the door behind me, and took a second to steady myself in front of the long, horizontal mirror that sat above the vanity. I turned on the cold water and splashed a little in my face, letting out a long exhale. Holy shit, I thought, what am I doing? I must still be really turned on from earlier to be misreading simple, normal situations like that. Cori did look hot as fuck tonight though. She was wearing a black, low cut top. While it didn't really show off any cleavage because of the size of her tits, they did prominently display how nice and perky they were. I wasn't sure exactly the size of them, but they looked like a perfect handful. And that ass...that black, lacy thong tucked up in between her ass cheeks; I couldn't take it anymore. I whipped out my phone and quickly opened my photos app, navigating to my hidden folder where I kept all of the nudes that Katie had sent me. I undid my belt and pulled my pants down just enough so I could set my cock free. I wasn't huge by any means, but I had a nice, girthy six inches. One thing was for sure, I thought, if that had been me with Cori there's no way I wouldn't have been able to get it up.

Scrolling through the vast collection of nudes I had of Katie, I found one of my favorites: a black and white photo of her looking directly into the camera, her huge tits being cupped by her arms and one of the sexiest looks on her face I had ever seen. I took my thick, hard cock in my hand and started stroking. The rush of pleasure started washing over me almost immediately; there was no way this was going to take long. I spit a little into my hand to give my cock a little bit of lube, and began running my hand up and down my shaft and over the tip. Every time my hand went back up towards the tip, I could feel a nice thick glob of precum dribble out of my cock, and I quickly spread it over the head and down my shaft, using it as extra lube. It wasn't long before I felt my balls begin to tighten and swell, and I knew I was going to cum soon. I put my phone down and leaned back into the vanity, throwing my head back as I was preparing for climax. Just as I was getting ready to cum, the sight of Cori's ass, sheer and exposed thanks to the perfect lighting flashed into my imagination. I began to shake a little as I pictured what it would feel like to bend her over and shove my cock deep inside of her tight, wet cunt and fuck her doggystyle. I imagined taking her hair in one hard and pulling her head back, hearing her moan in ecstasy as she felt my cock fill her up.I thought about how amazing her ass must look as it bounced back on my cock, pressing me harder and deeper into her pussy. I started to think about how amazing it would feel to have her orgasm while I'm inside of her, to feel the walls of her pussy spasming and milking every last drop of my cum out of my cock and into her. I wanted to fill her up, I wanted to make her mine, "Oh fuck, Cori. Oh shit, you like that you dirty little slut? You like having your best friend's fiance's cock pounding deep inside of you?" At that moment, my body locked up, and I felt rope after rope of cum explode from my cock. I tried my best to stifle my pleasure, but I know a few shuttered moans escaped my lips before I finally collapsed back into the vanity. I was slightly out of breath, and when I was finally able to open my eyes I could see that I had coated the floor with a hefty amount of thick white cum.